[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].Cl[CH2:10][O:11][CH3:12].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:10][O:11][CH3:12]To a solution of 2-bromophenol (5.0 g, 28.90 mmol) and chloro(methoxy)methane (3.4 g, 43.35 mmol) in DMF (50 mL) was added sodium carbonate (18.7 g, 57.8 mmol). The reaction mixture was heated at 80° C. for 12 h. After completion, the reaction mixture was diluted with water (100 mL) and extracted with ethyl acetate (2×100 mL). The organic layer was washed with water (3×100 mL), dried over sodium sulfate and concentrated under reduced pressure to yield desired 1-bromo-2-(methoxymethoxy)benzene (4.2 g, 67.7%) as a clear liquid, which was used without further purification.
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